Potassium Carbonate → Carbamic acid 3-[4-(1-phenyl-ethoxy)-phenyl]-isoxazol-5-ylmethyl ester

HRID 72317

Reaction equation

HRID 72317 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][O:14][C:15](=[O:17])[NH2:16])[O:10][N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26]>C(#N)C>[C:27]1([CH:25]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:12]=[C:11]([CH2:13][O:14][C:15](=[O:17])[NH2:16])[O:10][N:9]=3)=[CH:6][CH:7]=2)[CH3:26])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11454(1-Bromoethyl)benzeneHCID 136359907Carbamic acid 3-(4-hydroxy-phenyl)-isoxazol-5-ylmethyl ester

Product 1

HCID 46892361Carbamic acid 3-[4-(1-phenyl-ethoxy)-phenyl]-isoxazol-5-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Carbamic acid 3-(4-hydroxy-phenyl)-isoxazol-5-ylmethyl ester (150 mg, 0.64 mmol) and potassium carbonate (180 mg, 1.28 mmol) were dissolved in 10 ml of acetonitrile, to which was added dropwise (1-bromoethyl)benzene (131 μl, 0.96 mmol), and reacted at room temperature overnight. The completion of the reaction was confirmed by liquid chromatography, and then acetonitrile was distilled under reduced pressure. A crude solid compound was extracted with ethyl acetate and the solvent was distilled under reduced pressure to obtain a white solid compound. This was recrystallized from methylene chloride:MeOH (9:1) to obtain carbamic acid 3-[4-(1-phenyl-ethoxy)-phenyl]-isoxazol-5-ylmethyl ester as a white solid compound.

Workup

  1. customreacted at room temperature overnight
  2. distillationacetonitrile was distilled under reduced pressure
  3. extractionA crude solid compound was extracted with ethyl acetate
  4. distillationthe solvent was distilled under reduced pressure
  5. customto obtain a white solid compound
  6. customThis was recrystallized from methylene chloride:MeOH (9:1)

Sources & evidence

ORD record
ord-3ace41c4f3f84e0e83ec6a2a10f9b812
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Linked notes

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